Sodium hydride → 8-(6-Formylnaphthalen-2-yloxy)octanoic acid

HRID 1361002Notes

Reaction equation

HRID 1361002 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].[Na].C1([O-])C2C(=CC=CC=2)C=CC=1>CN(C=O)C.C(O)(=O)C>[CH:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:11]=[CH:10]2)=[O:13]

Participants

8

Reactant 5

HCID 24758Sodium hydride2×HCID 5482758-Bromooctanoic acidHCID 27641106-Hydroxy-2-naphthaldehydeHCID 5360545SodiumHCID 12168161Naphtholate

Product 1

HCID 574570398-(6-Formylnaphthalen-2-yloxy)octanoic acidYield 56.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The intermediate aldehyde for this compound was prepared by a slightly modified procedure: 6-Hydroxynaphthalene-2-carbaldehyde (1.0 g, 5.8 mmol) was dissolved in DMF (10 mL) and sodium hydride 60% (278 mg) was added and the mixture stirred at RT for 15 min. 8-Bromooctanoic acid (0.37 g, 1.7 mmol) was converted to the sodium salt by addition of sodium hydride 60% and added to an aliquot (2.5 mL) of the above naphtholate solution and the resulting mixture was stirred at RT for 16 hours. Aqueous acetic acid (10%) was added and the mixture was extracted 3 times with diethyl ether. The combined organic phases were dried with MgSO4 and evaporated to dryness affording 300 mg of 8-(6-formylnaphthalen-2-yloxy)octanoic acid.

Workup

  1. stirringthe resulting mixture was stirred at RT for 16 hours
  2. extractionthe mixture was extracted 3 times with diethyl ether
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7160a50037724d7182b890bf5e632b28
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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